Pyridazine compound

Abstract

A pyridazine compound represented by formula (1): wherein A represents a nitrogen atom or a CR 6 , R 1 represents a C2-C10 alkyl group having one or more halogen atoms, etc., R 2 and R 3 represent independently of each other a hydrogen atom, etc., R 4 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R 5 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, etc., R 6 represents a hydrogen atom, etc., n represents 0, 1, or 2, and p represents 0, 1, or 2, has an excellent efficacy for controlling harmful arthropods.

The invention claimed is: 
     
       1. A pyridazine compound represented by formula (1): 
       
         
           
           
               
               
           
         
         wherein,
 A represents a nitrogen atom or a CR 6 ; 
 R 1  represents a C2-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, a (C1-C5 alkyl)-O—(C2-C5 alkyl) group, a (C3-C5 alkenyl)-O—(C2-C5 alkyl) group, a (C3-C5 alkynyl)-O—(C2-C5 alkyl) group, a (C1-C5 alkyl)-S(O) m —(C2-C5 alkyl) group, a (C3-C5 alkenyl)-S(O) m —(C2-C5 alkyl) group, a (C3-C5 alkynyl)-S(O) m —(C2-C5 alkyl) group, or a (C1-C5 alkyl)-C(O)—(C1-C5 alkyl) group, wherein R 1  has one or more halogen atoms; 
 R 2  and R 3  represent independently of each other a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group, a cyano group, or a halogen atom; 
 R 4  represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms; 
 R 5  represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more atoms or groups selected from Group A, a 5-membered aromatic heterocyclic group selected from Group B, wherein said 5-membered aromatic heterocyclic group may optionally have one or more atoms or groups selected from Group A, a 6-membered aromatic heterocyclic group selected from Group C, wherein said 6-membered aromatic heterocyclic group may optionally have one or more atoms or groups selected from Group A, a 3 to 7 membered nonaromatic heterocyclic group selected from Group D, wherein the 3 to 7 membered nonaromatic heterocyclic group may optionally have one or more atoms or groups selected from the group consisting of a halogen atom and a C1-C6 alkyl group, a OR 7 , a NR 8 R 9 , a NR 8 C(O)R 10 , a NR 8 C(O)OR 11 , a NR 8 C(O)NR 12 R 13 , a N═CHNR 12 R 13 , a N═S(O)R 12 R 13 , a S(O) y R 12 , a C(O)OR 8 , a cyano group, or a halogen atom; 
 R 6  represents a hydrogen atom, or a halogen atom; 
 R 7  represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a (C1-C3 alkyl)-O—(C1-C3 alkyl) group, a (C1-C3 alkyl)-S(O) y —(C1-C3 alkyl) group, a C3-C7 cycloalkyl group, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, wherein said C1-C6 alkyl group, said C3-C6 alkenyl group, said C3-C6 alkynyl group, said (C1-C3 alkyl)-O—(C1-C3 alkyl) group, said (C1-C3 alkyl)-S(O) y —(C1-C3 alkyl) group, said C3-C7 cycloalkyl group, and said (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may optionally have one or more halogen atoms, or a phenyl C1-C3 alkyl group, wherein the phenyl moiety in said phenyl C1-C3 alkyl group may optionally have one or more atoms or groups selected from Group A; 
 R 8  represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, or a C3-C6 alkynyl group optionally having one or more halogen atoms; 
 R 9  represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a (C1-C3 alkyl)-O—(C1-C3 alkyl) group, a (C1-C3 alkyl)-S(O) y —(C1-C3 alkyl) group, a C3-C7 cycloalkyl group, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, wherein said C1-C6 alkyl group, said C3-C6 alkenyl group, said C3-C6 alkynyl group, said (C1-C3 alkyl)-O—(C1-C3 alkyl) group, said (C1-C3 alkyl)-S(O) y —(C1-C3 alkyl) group, said C3-C7 cycloalkyl group, and said (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may optionally have one or more halogen atoms, 
 a cyano C1-C6 alkyl group, 
 a phenyl C1-C3 alkyl group, wherein the phenyl moiety in said phenyl C1-C3 alkyl group may optionally have one or more atoms or groups selected from Group A, or 
 a (5 or 6 membered heteroaryl)C1-C3 alkyl group, wherein the 5 or 6 membered heteroaryl moiety in said (5 or 6 membered heteroaryl)C1-C3 alkyl group may optionally have one or more atoms or groups selected from Group A; 
 R 10  represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C3-C7 cycloalkyl group, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, wherein said C1-C6 alkyl group, said C3-C6 alkenyl group, said C3-C6 alkynyl group, said C3-C7 cycloalkyl group, and said (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may optionally have one or more halogen atoms, or a phenyl C1-C3 alkyl group, wherein the phenyl moiety in said phenyl C1-C3 alkyl group may optionally have one or more atoms or substituents selected from Group A; 
 R 11  represents a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, a C3-C6 alkynyl group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group optionally having one or more halogen atoms, wherein said (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may optionally have one or more halogen atoms, or a phenyl C1-C3 alkyl group, wherein the phenyl moiety in said phenyl C1-C3 alkyl group may optionally have one or more atoms or groups selected from Group A; 
 R 12  and R 13  represent independently of each other a C1-C6 alkyl group optionally having one or more halogen atoms; 
 R 14  represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, or a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms; 
 n represents 0, 1, or 2; 
 m represents 0, 1, or 2; 
 p represents 0, 1, 2, or 3, wherein when p represents 2 or 3, a plurality of R 5  may be identical or different; 
 x represents 0 or 1; 
 y represents 0, 1, or 2; 
 Group A: a group consisting of a C1-C6 alkyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a cyano group, and a halogen atom; 
 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       2. The compound according to  claim 1 , wherein A represents CR 6 . 
     
     
       3. The compound according to  claim 1 , wherein A represents a nitrogen atom. 
     
     
       4. The compound according to  claim 1 , wherein R 4  represents a C1-C6 alkyl group optionally having one or more halogen atoms. 
     
     
       5. The compound according to  claim 1 , wherein R 4  represents an ethyl group. 
     
     
       6. The compound according to  claim 1 , wherein
 R 1  represents a C2-C10 haloalkyl group; 
 R 2  and R 3  represent independently of each other a hydrogen atom, a C1-C3 alkyl group optionally having one or more halogen atoms, or a halogen atom; 
 R 4  represents a C1-C6 alkyl group optionally having one or more halogen atoms; 
 R 5  represents a C1-C6 alkyl group optionally having one or more halogen atoms; and 
 p represents 0 or 1. 
 
     
     
       7. The compound according to  claim 1 , wherein
 R 1  represents a C2-C10 haloalkyl group; 
 R 2  and R 3  represent each a hydrogen atom; 
 R 4  represents a C1-C6 alkyl group optionally having one or more halogen atoms; 
 R 5  represents a C1-C6 alkyl group optionally having one or more halogen atoms; and 
 p represents 0 or 1. 
 
     
     
       8. The compound according to  claim 1 , wherein
 R 1  represents a C3-C6 alkyl having four or more fluorine atoms; 
 R 2  and R 3  represent each a hydrogen atom; 
 R 4  represents an ethyl group; 
 R 5  represents a C1-C6 alkyl group optionally having one or more halogen atoms; and 
 p represents 0 or 1. 
 
     
     
       9. A compound represented by formula (1-N): 
       
         
           
           
               
               
           
         
         wherein
 Q 1  represents a N + —O −  or a nitrogen atom, 
 Q 2  represents a N + —O − , a CR 6N , or a nitrogen atom, 
 wherein at least one of Q 1  and Q 2  represents an N + —O − ; 
 R 6N  represents a hydrogen atom, or a halogen atom; 
 R 1N  represents a C2-C10 haloalkyl group; 
 R 2N  and R 3N  represent independently of each other a hydrogen atom, a C1-C3 alkyl group optionally having one or more halogen atoms, or a halogen group; 
 R 4N  represents a C1-C6 alkyl group optionally having one or more halogen atoms; 
 R 5N  represents a C1-C6 alkyl group optionally having one or more halogen atoms; and 
 q represents 0 or 1. 
 
       
     
     
       10. A composition for controlling a harmful arthropod, comprising the compound according to  claim 1 , and an inert carrier. 
     
     
       11. A method for controlling a harmful arthropod, comprising applying an effective amount of the compound according to  claim 1  to a harmful arthropod or a habitat where a harmful arthropod lives. 
     
     
       12. A composition for controlling a harmful arthropod, comprising the compound according to  claim 9 , and an inert carrier. 
     
     
       13. A method for controlling a harmful arthropod, comprising applying an effective amount of the compound according to  claim 9  to a harmful arthropod or a habitat where a harmful arthropod lives.